KR20240105869A - Organic compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device using the same. More specifically, it relates to an organic compound having excellent electron transport ability, heat resistance, carrier transport ability, and luminescence ability, and including the same in one or more organic layers to increase luminous efficiency, This is about an organic electroluminescent device with improved characteristics such as driving voltage and lifespan.

Description

Organic compounds and organic electroluminescent devices using the same {ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME}

The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more specifically, to an organic compound having excellent electron transport ability, heat resistance, carrier transport ability, and luminescence ability, and including the same in one or more organic layers to increase luminous efficiency, It relates to an organic electroluminescent device with improved characteristics such as driving voltage and lifespan.

When a voltage is applied between two electrodes in an organic electroluminescent device (hereinafter referred to as an 'organic EL device'), holes are injected into the organic material layer from the anode, and electrons are injected into the organic material layer from the cathode. When the injected hole and electron meet, an exciton is formed, and when this exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into light-emitting material, hole injection material, hole transport material, electron transport material, electron injection material, etc., depending on its function.

Light-emitting materials can be divided into blue, green, and red light-emitting materials according to their emission color, and yellow and orange light-emitting materials to achieve better natural colors. Additionally, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system can be used as a luminescent material.

Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. At this time, because the development of phosphorescent materials can theoretically improve luminous efficiency by up to four times compared to fluorescence, much research is being conducted on phosphorescent host materials as well as phosphorescent dopants.

So far, hole injection layer and hole transport layer. NPB, BCP, Alq ₃ , etc. are widely known as hole blocking layer and electron transport layer materials, and anthracene derivatives are reported as light emitting layer materials. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy) ₃ , and (acac)Ir(btp) ₂ , which have advantages in terms of efficiency improvement among light emitting layer materials, produce blue, green, and red colors. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.

However, although conventional organic layer materials are advantageous in terms of luminescent properties, their glass transition temperature is low and their thermal stability is very poor, so they are not at a satisfactory level in terms of the lifespan of organic electroluminescent devices. Therefore, the development of organic layer materials with excellent performance is required.

The present invention provides a novel compound that has excellent electron transport ability, heat resistance, carrier transport ability, luminescence ability, etc., and can be used as an organic layer material of an organic electroluminescent device, specifically an electron transport layer material or an electron transport auxiliary layer material, etc. The purpose.

Another object of the present invention is to provide an organic electroluminescent device containing the novel compound, which has low driving voltage, high luminous efficiency, excellent electrical stability, and improved lifespan.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1):

(In Formula 1 above,

X ₁ to X _{3 are} the same or different from each other and are each independently N or C(R ₃ ), provided that at least two of X ₁ to

a is 2 or 3,

A plurality of R ₁ is the same or different from each other, and each independently represents deuterium, a cyano group, a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group of 3 to 40 nuclear atoms, an aryl group of C ₆ to C ₆₀ , and a nucleus. selected from the group consisting of heteroaryl groups having 5 to 60 atoms, or condensed with adjacent groups to form a condensed ring,

Ar ₁ is hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , C ₆ to C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) amine group and hetero of 5 to 60 nuclear atoms selected from the group consisting of an arylamine group,

n is an integer from 0 to 5,

L ₁ is a single bond or is selected from the group consisting of a C ₁ ~ C ₆₀ alkylene group, a C ₆ ~ C ₆₀ arylene group, and a heteroarylene group with 5 to 60 nuclear atoms,

Y ₁ is selected from the group consisting of O, S, C(R ₄ )(R ₅ ) and N(R ₆ ),

Y ₂ is a single bond or selected from the group consisting of O, S, C(R ₇ )(R ₈ ) and N(R ₉ ),

b is an integer from 0 to 7,

R ₂ to R ₉ are the same or different from each other, and each independently represents hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl ) is selected from the group consisting of an amine group and a heteroarylamine group having 5 to 60 nuclear atoms, or is condensed with an adjacent group to form a condensed ring,

The cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group and condensed ring of R ₁ , the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group and alkyloxy group of Ar ₁ , aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, aryl amine group, (aryl) (heteroaryl) amine group and heteroaryl amine group, The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl of R ₂ to R ₉ A boron group, an arylphosphine group, an arylphosphine oxide group, an arylamine group, (aryl)(heteroaryl)amine group, a heteroarylamine group, and a condensed ring, and the alkylene group, arylene group, and heteroarylene of L ₁ The groups are each independently deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group , heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group. Period, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphos Pin group, C ₆ to C ₆₀ arylphosphine oxide group, C ₆ to C ₆₀ arylamine group, C ₆ to C ₆₀ (aryl) (heteroaryl) amine group and heteroarylamine with 5 to 60 nuclear atoms. It is substituted or unsubstituted with one or more substituents selected from the group consisting of groups, or the substituents condense with adjacent groups to form a condensed ring. In this case, when the substituents are plural, they are the same or different from each other.

In addition, the present invention is an anode; cathode; Provided is an organic electroluminescent device comprising one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers including the compound represented by the above-mentioned formula (1).

According to one example, the organic material layer containing the compound may be at least one selected from the group consisting of an electron transport layer and an electron transport auxiliary layer.

Since the compound of the present invention is excellent in electron transport ability, heat resistance, carrier transport ability, luminescence ability, etc., it can be used as an organic layer material of an organic electroluminescent device. In particular, when the compound of the present invention is used as an electron transport layer material or an electron transport auxiliary layer material, an organic electroluminescent device can be manufactured with excellent light emission performance, low driving voltage, high efficiency, and long life characteristics compared to conventional materials. Full-color display panels with improved performance and lifespan can also be manufactured.

The effects according to the present invention are not limited to the contents exemplified above, and more diverse effects are included in the present specification.

1 is a cross-sectional view schematically showing an organic electroluminescent device according to a first embodiment of the present invention.
Figure 2 is a cross-sectional view schematically showing an organic electroluminescent device according to a second embodiment of the present invention.
Figure 3 is a cross-sectional view schematically showing an organic electroluminescent device according to a third embodiment of the present invention.

Hereinafter, the present invention will be described.

<New compound>

The new compound according to the present invention is a dibenzo moiety and a nitrogen-containing heteroaromatic ring bonded directly or through a linker, and the nitrogen-containing heteroaromatic ring has a benzene ring substituted with 2 to 3 substituents (e.g., terphenyl group, etc.) It is a structure composed of bonds, and is represented by the formula 1 above. The compound of the present invention has excellent thermal stability, carrier transport ability (e.g., electron transport ability), and luminescence ability, and is an organic material layer material capable of realizing the characteristics of an organic electroluminescent device, such as high efficiency, long life, and low driving voltage of the device. , In particular, it can be used as an electron transport layer material or an electron transport auxiliary layer.

Typically, in an organic electroluminescent device, as the injection of electrons from the electron transport layer to the light emitting layer becomes faster, the lifespan of the device tends to decrease. This is a phenomenon that occurs locally where excitons are formed in the light-emitting layer. To solve this problem, the electron injection rate must be adjusted. However, if the electron injection rate is simply slowed down, the efficiency of the blue organic electroluminescent device decreases. Therefore, the injection speed of electrons injected into the light-emitting layer must be maintained quickly and the electron transport ability must be controlled so that excitons are formed uniformly in the entire area of the light-emitting layer. Accordingly, in the compound represented by Formula 1 according to the present invention, the dibenzo moiety and the nitrogen-containing heteroaromatic ring are bonded directly or through a linker. At this time, a benzene ring (e.g., terphenyl group, etc.) substituted with 2 to 3 substituents (e.g., aryl group, cycloalkyl group, heteroaryl group, cyano group, etc.) is bonded (introduced) to the nitrogen-containing heteroaromatic ring. . In the compound of the present invention, the dibenzo moiety is a fluorene moiety, an oxanthrene moiety, etc., and can improve conductivity. Additionally, nitrogen-containing heteroaromatic rings are six-membered heteroaromatic rings containing two or three nitrogen (N) elements, and include pyrimidine and triazine. This nitrogen-containing heteroaromatic ring is an electron attractor (EWG) with high electron absorption, and the electron transfer speed is improved, thereby improving electron transport ability. In addition, the benzene ring substituted with 2 to 3 substituents can control the stability of the molecule and the electron transport rate of the material. Therefore, the compound of the present invention has LUMO energy that facilitates electron injection into the light-emitting layer, and the electron transport ability is improved by the combination of a dibenzo moiety and a benzene ring substituted with 2 to 3 substituents, making it superior to conventional electron transport layer materials. Compared to this, high efficiency and long life characteristics of the device can be realized. In addition, the compound of the present invention not only has excellent chemical stability, but also has a high Excellent thermal stability due to glass transition temperature (Tg). The present invention can have physicochemical properties more suitable for electron injection and electron transport due to the nitrogen-containing heteroaromatic ring.

In addition, since the compound represented by Formula 1 of the present invention has a higher triplet energy than the light-emitting layer, it can prevent excitons generated in the light-emitting layer from diffusing (moving) to the adjacent electron transport layer or hole transport layer. Therefore, the compound of the present invention can improve the luminous efficiency of the device by increasing the number of excitons contributing to light emission in the light-emitting layer, and improve the durability and stability of the device, thereby efficiently increasing the lifespan of the device. In addition, the organic electroluminescent device to which the compound of the present invention is applied can be driven at low voltage, so its lifespan can be improved.

As described above, the compound represented by Formula 1 of the present invention is used as an organic material layer material of an organic electroluminescent device, specifically a light-emitting layer material (blue, green, and/or red phosphorescent host material), an electron transport layer/injection layer material, and a hole transport layer. /When applied as an injection layer material, a light-emitting auxiliary layer material, an electron transport auxiliary layer material, or a lifespan improvement layer material, more specifically, an electron transport layer material or an electron transport auxiliary layer material, the performance and lifespan characteristics of an organic electroluminescent device are greatly improved. It can be. These organic electroluminescent devices can ultimately maximize the performance of full-color organic light emitting panels.

In the compound represented by Formula 1, X ₁ to X _{3 are} the same or different from each other and are each independently N or C(R ₃ ), provided that at least two of X ₁ to These X _{1 to} As a result, the compound of Formula 1 according to the present invention exhibits better electron absorption properties and may be advantageous for electron injection and transport.

According to one example, the X ₁ to X ₃ -containing ring moiety ( ) may be selected from the group consisting of the following moieties Az-1 to Az-3.

In the moieties Az-1 to Az-3,

* refers to the part where a bond is formed with Formula 1,

Ar ₁ , a, R ₁ and R ₃ are each as defined in Formula 1 above.

R ₃ is hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) amine group and 5 to 60 nuclear atoms It is selected from the group consisting of a heteroarylamine group, or is condensed with an adjacent group (e.g. R ₃ -Ar ₁ , R ₃ -R ₁ , R ₃ -L ₁ ) to form a condensed ring, and specifically, R ₃ is hydrogen. , deuterium, halogen group, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group. , a heteroaryl group having 5 to 60 nuclear atoms, and an arylamine group having C ₆ to C ₆₀ .

At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron of R ₃ group, arylphosphine group, arylphosphine oxide group, arylamine group, (aryl)(heteroaryl)amine group, heteroarylamine group, and condensed ring are each independently deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ Substituted or unsubstituted with one or more substituents selected from the group consisting of an arylamine group of ~ _C60 , an (aryl)(heteroaryl)amine group of _C6 ~ _C60 , and a heteroarylamine group of 5 to 60 nuclear atoms, Or, the substituent condenses with an adjacent group to form a condensed ring, specifically deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, number of nuclear atoms 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 nuclear atoms heteroaryl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, and C ₆ It may be substituted or unsubstituted with one or more substituents selected from the group consisting of ~C ₆₀ arylamine groups, and in this case, when the substituents are plural, they are the same or different from each other.

In the compound represented by Formula 1, a is 2 or 3.

Here, when a is 2 or 3, it means that hydrogen is replaced with a substituent R ₁ .

A plurality of R ₁ is the same or different from each other, and each independently represents a deuterium (D), a cyano group (-CN), a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group of 3 to 40 nuclear atoms, and C ₆ to C It is selected from the group consisting of an aryl group of ₆₀ and a heteroaryl group of 5 to 60 nuclear atoms, or condensed with an adjacent group (e.g., a benzene ring to which R ₁ -R ₁ and R ₁ -R ₁ are bonded) to form a condensed ring. forms. Here, the condensed ring may be a condensed aromatic ring of C ₆ to C ₃₀ or a condensed heteroaromatic ring of 5 to 30 nuclear atoms containing one or more heteroatoms (e.g., N, O, S, Se, etc.). there is.

At this time, the cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, and condensed ring of R ₁ are each independently deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, 5 to 60 nuclear atoms Heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C _{6 ~ C 60 arylphosphine oxide group, C 6 ~ C 60 arylamine group} , C ₆ ~ C A group that is substituted or unsubstituted with one or more substituents (R) selected from the group consisting of ₆₀ (aryl) (heteroaryl) amine groups and heteroarylamine groups with 5 to 60 nuclear atoms, or to which the substituent (R) is adjacent. (e.g. RR, RR ₁ ) and condensation to form a condensed ring, specifically, deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₃ to C ₄₀ cycloalkyl group, and 3 to 40 nuclear atoms. Heterocycloalkyl group, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, and C ₆ to C ₆₀ is substituted or unsubstituted with one or more substituents (R) selected from the group consisting of an arylamine group, or the substituent (R) is condensed with an adjacent group (e.g. RR, RR ₁ ) to form a condensed ring, and the substituents If there is a plurality of , they are the same or different from each other.

Depending on R ₁ , the compound represented by Formula 1 may be a compound represented by Formula 2 or 3 below. However, it is not limited to this.

In Formulas 2 and 3,

X ₁ to X ₃ , Ar ₁ , n, L ₁ , Y ₁ , Y ₂ , b, R ₂ are each as defined in Formula 1 above,

c1 and c2 are each integers from 0 to 5,

d is 0 or 1,

Q ₁ to Q ₆ are the same or different from each other, and are each independently N or C(Ar ₆ ), provided that at least one of Q ₁ to Q ₆ is N, and specifically, at least one of Q ₁ to Q ₃ is N and the remainder may be C(Ar ₆ ), or at least one of Q ₄ to Q ₆ may be N and the remainder may be C(Ar ₆ ),

R _10, R ₁₁ and Ar ₂ to Ar ₆ are the same or different from each other, and each independently represents deuterium, halogen, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) amine group and heteroarylamine group having 5 to 60 nuclear atoms, or adjacent groups (e.g. R ₁₀ -R ₁₀ , R ₁₀ -R ₁₁ , R ₁₁ -R ₁₁ , etc.) Condensation forms a condensed ring, and specifically, each independently deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ ~C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, and C ₆ ~C ₆₀ arylamine group, or adjacent groups (e.g. R ₁₀ -R ₁₀ , R ₁₀ -R ₁₁ , R ₁₁ -R ₁₁ , etc.) can be condensed to form a condensed ring,

Ar ₂ to Ar ₆ alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl Boron group, arylphosphine group, arylphosphine oxide group, arylamine group, (aryl)(heteroaryl)amine group, heteroarylamine group and condensed ring are each independently deuterium, halogen, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ Substituted or unsubstituted with one or more substituents selected from the group consisting of a C ₆₀ arylamine group, a C ₆ to C ₆₀ (aryl) (heteroaryl) amine group, and a heteroarylamine group having 5 to 60 nuclear atoms, or The substituents condense with adjacent groups to form a condensed ring, and when there are multiple substituents, they are the same or different from each other.

According to one example, The moiety may be selected from the group consisting of the following moieties Mo1-1 to Mo1-15. However, it is not limited to this.

In the moieties Mo1-1 to Mo1-15,

* refers to the part where a bond is formed with Formula 1,

d, m1 and m2 are 0 or 1 respectively,

c3 to c7 are each an integer from 0 to 5, provided that 1≤c3+c4≤10, 1≤c5+c6≤10,

c8 is an integer from 0 to 4,

c9 is an integer from 0 to 8,

c10 is an integer from 0 to 6,

R ₁₂ and R ₁₃ are the same as or different from each other, and are each independently selected from the group consisting of a cyano group, an alkyl group of C ₁ to C ₄₀ and a heteroaryl group of 5 to 60 nuclear atoms,

Z ₁ is selected from the group consisting of O, S, C(R ₁₅ )(R ₁₆ ) and N(R ₁₇ ),

Z ₂ to Z ₁₃ are the same or different from each other, and are each independently a single bond or selected from the group consisting of O, S, C(R ₁₈ )(R ₁₉ ) and N(R ₂₀ ),

X ₄ to X _{7 are} the same or different from each other and are each independently N or C(R ₂₁ ), provided that at least one of X ₄ to

Ring Cy1 to Cy3 are the same or different from each other, and are each independently selected from the group consisting of a fused aromatic ring of C ₆ to C ₃₀ and a fused heteroaromatic ring of 5 to 30 nuclear atoms,

One or more R ₁₄ are the same or different from each other, and are each independently selected from the group consisting of an aryl group of C ₆ to C ₃₀ and a heteroaryl group of 5 to 30 nuclear atoms,

R ₁₅ to R ₂₁ are the same or different from each other, and are each independently hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) It is selected from the group consisting of an amine group and a heteroarylamine group having 5 to 60 nuclear atoms, or is condensed with an adjacent group (e.g. R ₁₅ -R ₁₆ , R ₁₈ -R ₁₉ , etc.) to form a condensed ring, specifically Hydrogen, deuterium, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl with 5 to 60 nuclear atoms group, and an arylamine group of C ₆ to C ₆₀ , or may be condensed with an adjacent group (e.g., R ₁₅ -R ₁₆ , R ₁₈ -R ₁₉ , etc.) to form a condensed ring.

According to another example, the above The moiety may be selected from the group consisting of the following moieties Mo2-1 to Mo2-67. However, it is not limited to this.

In the moieties Mo2-1 to Mo2-67,

* refers to the part where a bond is formed with Formula 1,

c8 is 0 or 1,

Ring Cy1 to Ring Cy3 are each as defined in the above moieties Mo1-1 to Mo1-15, are specifically the same as or different from each other, and are each independently a C ₆ to C ₂₀ fused aromatic ring or a nuclear atom number of 5 to 20. It may be a condensed heteroaromatic ring.

The hydrogen of the above-mentioned moieties Mo2-1 to Mo2-67 is deuterium (D), halogen, nitro group, C ₁ to C ₁₂ alkyl group, C ₆ to C ₁₀ aryl group, and heterogeneous group with 5 to 10 nuclear atoms. It may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group.

In the compound represented by Formula 1, Ar ₁ is hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyl Oxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl Boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) amine group and heteroarylamine groups having 5 to 60 nuclear atoms, specifically hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₃ to C ₄₀ cyclo It may be selected from the group consisting of an alkyl group, a heterocycloalkyl group with 3 to 40 nuclear atoms, an aryl group with C ₆ to C ₆₀ , a heteroaryl group with 5 to 60 nuclear atoms, and an arylamine group with C ₆ to C ₆₀ .

At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, and arylboron of Ar ₁ group, arylphosphine group, arylphosphine oxide group, arylamine group, (aryl)(heteroaryl)amine group, and heteroarylamine group are each independently deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, Heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group , C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ aryl Substituted or unsubstituted with one or more substituents selected from the group consisting of an amine group, a C ₆ to C ₆₀ (aryl) (heteroaryl) amine group, and a heteroarylamine group having 5 to 60 nuclear atoms, or the substituent is adjacent to It condenses with a group to form a condensed ring, specifically deuterium, halogen, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₃ to C ₄₀ cycloalkyl group, and heterocycloalkyl group with 3 to 40 nuclear atoms. , C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, and C ₆ ~ C ₆₀ arylamine group. may be substituted or unsubstituted with one or more substituents selected from the group consisting of, and when the substituents are plural, they may be the same or different from each other.

According to one example, Ar ₁ may be selected from the group consisting of the following substituents S1 to S23. However, it is not limited to this.

In the substituents S1 to S23,

* refers to the part where a bond is formed with Chemical Formula 1.

The hydrogen of the above-mentioned substituents S1 to S23 is from the group consisting of deuterium (D), halogen, nitro group, C ₁ to C ₁₂ alkyl group, C ₆ to C ₁₀ aryl group, and heteroaryl group with 5 to 10 nuclear atoms. It may be substituted or unsubstituted with one or more selected substituents.

In the compound represented by Formula 1, n is an integer from 0 to 5, and may specifically be an integer from 1 to 4.

Here, when n is 0, L ₁ means a direct bond (single bond). On the other hand, when n is an integer of 1 to 5, L ₁ is a divalent linker group, such as an alkylene group of C ₁ to C ₆₀ , an arylene group of C ₆ to C ₆₀ and a heteroaryl group of 5 to 60 nuclear atoms. It may be selected from the group consisting of a lene group, and specifically may be selected from the group consisting of a C ₁ to C ₁₈ alkylene group, a C ₆ to C ₁₈ arylene group, and a heteroarylene group with 5 to 18 nuclear atoms. Here, the plurality of L ₁ may be the same or different from each other.

The alkylene group, arylene group, and heteroarylene group of L ₁ are each independently deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) It is substituted or unsubstituted with one or more substituents selected from the group consisting of an amine group and a heteroarylamine group having 5 to 60 nuclear atoms, or the substituent condenses with an adjacent group to form a condensed ring, and in this case, the substituent is plural. , they are the same or different from each other.

According to one example, one or more L ₁ may be the same or different from each other, and may each independently be a single bond or a C ₆ to C ₁₈ arylene group.

According to another example, one or more L ₁ are the same or different from each other, and are each independently a single bond, or a phenylene group, a biphenylene group, a terphenylene group, a naphthalene group, a phenanthrene group, a triphenylene group, or a fluorene group. and combinations thereof. Here, the hydrogen of the phenylene group, biphenylene group, terphenylene group, naphthalene group, phenanthrene group, triphenylene group, and fluorene group is deuterium (D), halogen (e.g. -F, -Cl, -Br, -I etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), C ₁ to C ₁₂ alkyl group, C ₆ to C ₁₀ aryl group, and 5 to 10 nuclear atoms. It may be substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl groups.

According to another example, one or more L ₁ may be the same or different from each other, and each independently may be a single bond, or may be selected from the group consisting of the following linker groups L1-1 to L1-3. However, it is not limited to this.

In the linker groups L1-1 to L1-3,

* refers to the part where a bond is formed with Formula 1,

e is an integer from 0 to 4,

One or more R ₂₂ are the same or different from each other, and each independently represents hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl ) is selected from the group consisting of amine groups and heteroarylamine groups having 5 to 60 nuclear atoms, specifically deuterium, halogen, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₃ to C ₄₀ cyclo Alkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkylsilyl group with C ₁ to C ₄₀ , aryl with C ₆ to C ₆₀ It may be selected from the group consisting of a silyl group and an arylamine group of C ₆ to C ₆₀ .

According to another example, the above The moiety may be selected from the group consisting of the following linker groups L2-1 to L2-44. However, it is not limited to this.

In the linker groups L2-1 to L2-44,

* refers to the part where a bond is formed with Chemical Formula 1.

The hydrogen of the above-mentioned linker groups L2-1 to L2-44 is deuterium (D), halogen, nitro group, C ₁ to C ₁₂ alkyl group, C ₆ to C ₁₀ aryl group, and heterogeneous group with 5 to 10 nuclear atoms. It may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group.

In the compound represented by Formula 1, Y ₁ is selected from the group consisting of O, S, C(R ₄ )(R ₅ ) and N(R ₆ ), and Y ₂ is a single bond, or O, S, It is selected from the group consisting of C(R ₇ )(R ₈ ) and N(R ₉ ). At this time, Y ₁ and Y ₂ are the same or different from each other.

Additionally, in the compound represented by Formula 1, b is an integer from 0 to 7.

Here, when b is 0, it means that hydrogen is unsubstituted with a substituent R ₂ . Meanwhile, when b is an integer of 1 to 7, it means that hydrogen is substituted with a substituent R ₂ . A plurality of R ₂ may be the same as or different from each other.

R ₂ to R ₉ are the same as or different from each other, and are each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ ~C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (hetero Aryl) amine groups and heteroarylamine groups having 5 to 60 nuclear atoms, or adjacent groups (e.g. R ₂ -R ₂ . R ₂ -R ₄ , R ₂ -R ₅ , R ₂ - R ₇ , R ₂ -R ₉ , R ₄ -R ₅ , R ₇ -R ₈ ) and condensate to form a condensed ring, specifically and independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ ~ Is selected from the group consisting of C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, and C ₆ ~ C ₆₀ arylamine group, or an adjacent group (e.g. R ₂ -R _2. R ₂ -R ₄ , R ₂ -R ₅ , R ₂ -R ₇ , R ₂ -R ₉ , R ₄ -R ₅ , R ₇ -R ₈ ) and can form a condensed ring.

At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, and alkylboron group of R ₂ to R ₉ , aryl boron group, aryl phosphine group, aryl phosphine oxide group, aryl amine group, (aryl) (heteroaryl) amine group, heteroaryl amine group, and condensed ring are each independently deuterium, halogen, cyano group, and nitro group. , amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group , C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) amine group, and heteroarylamine group having 5 to 60 nuclear atoms. Substituted or provided with one or more substituents selected from the group consisting of ring, or the substituents condense with adjacent groups to form a condensed ring, and in this case, when the substituents are plural, they are the same or different from each other.

According to one example, Y ₁ and Y ₂ -containing ring moieties ( moiety) may be selected from the group consisting of the following moieties Mo3-1 to Mo3-17. However, it is not limited to this.

In the moieties Mo3-1 to Mo3-17,

Y _1, b and R ₂ are each as defined in Formula 1 above,

CyA and CyB are the same or different from each other, and are each independently selected from the group consisting of a fused aromatic ring of C ₆ to C ₃₀ and a fused heteroaromatic ring of 5 to 30 nuclear atoms,

b1 is an integer from 0 to 5,

b2 is an integer from 0 to 3,

f is an integer from 0 to 8,

f1 is an integer from 0 to 6,

f2 is an integer from 0 to 4,

R ₂₃ is hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ Cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , C ₆ to C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) amine group and hetero of 5 to 60 nuclear atoms selected from the group consisting of an arylamine group,

The condensed aromatic ring and condensed heteroaromatic ring of CyA and CyB are each independently deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) It is substituted or unsubstituted with one or more substituents selected from the group consisting of amine groups and heteroarylamine groups having 5 to 60 nuclear atoms. In this case, when the substituents are plural, they are the same or different from each other.

According to another example, the above The moiety may be selected from the group consisting of the following moieties Mo4-1 to Mo4-71. However, it is not limited to this.

In the moieties Mo4-1 to Mo4-71,

* refers to the part where a bond is formed with Formula 1,

CyA and CyB are the same or different from each other, and are each independently selected from the group consisting of a fused aromatic ring of C ₆ to C ₃₀ and a fused heteroaromatic ring of 5 to 30 nuclear atoms,

The condensed aromatic rings of CyA and CyB are each independently deuterium (D), a halogen group, a cyano group, an alkyl group of C ₁ to C ₄₀ , a cycloalkyl group of C ₃ to C ₄₀ , and a heterocycloalkyl group of 3 to 40 nuclear atoms. , C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, and C ₆ ~ C ₆₀ arylamine group. It is substituted or unsubstituted with one or more substituents selected from the group consisting of, and when the substituents are plural, they are the same or different from each other.

In addition, the hydrogen of the moieties Mo4-1 to Mo4-71 is deuterium (D), halogen group, cyano group, C ₁ to C ₄₀ alkyl group, C ₁ to C ₄₀ haloalkyl group, C ₃ to C ₄₀ cyclo. Alkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, aryl group with C ₆ to C ₆₀ (e.g. phenyl group, biphenyl group, etc.), heteroaryl group with 5 to 60 nuclear atoms (e.g. carbazole group, phenoxazine, oxatrene, etc.), C ₁ to C ₄₀ alkylsilyl group (e.g., methylsilyl group, etc.), C ₆ to C ₆₀ arylsilyl group (e.g., phenylsilyl group, etc.), and C ₆ to C ₆₀ arylamine group. It may be substituted or unsubstituted with one or more substituents selected from the group consisting of, and in this case, when the substituents are plural, they are the same or different from each other.

Depending on Y ₁ , Y ₂ and R ₁ , the compound represented by Formula 1 may be a compound represented by any one of Formulas 4 to 37 below. However, it is not limited to this.

In Formulas 4 to 37,

X ₁ to X ₃ , Y ₁ , Ar ₁ , n, L ₁ , b, R ₂ are each as defined in Formula 1 above,

CyA and CyB are the same or different from each other, and are each independently selected from the group consisting of a fused aromatic ring of C ₆ to C ₃₀ and a fused heteroaromatic ring of 5 to 30 nuclear atoms,

b1 is an integer from 0 to 5,

b2 is an integer from 0 to 3,

c1 and c2 are each integers from 0 to 5,

d is 0 or 1,

f is an integer from 0 to 8,

f1 is an integer from 0 to 6,

f2 is an integer from 0 to 4,

Q ₁ to Q ₆ are the same or different from each other and are each independently N or C(Ar ₆ ), provided that at least one of Q ₁ to Q ₆ is N,

R _10, R ₁₁ and Ar ₂ to Ar ₆ are the same or different from each other, and each independently represents deuterium, halogen, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) is selected from the group consisting of an amine group and a heteroarylamine group having 5 to 60 nuclear atoms, or is condensed with an adjacent group to form a condensed ring,

R ₂₃ is hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ Cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , C ₆ to C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) amine group and hetero of 5 to 60 nuclear atoms selected from the group consisting of an arylamine group,

CyA and the condensed aromatic ring and condensed heteroaromatic ring of CyA, and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, and aryloxy group of Ar ₂ to Ar ₆ Group, alkyl silyl group, aryl silyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, aryl amine group, (aryl) (heteroaryl) amine group, heteroaryl amine group and condensed ring are each Independently deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nucleus Heterocycloalkyl group with 3 to 40 atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, Consists of an arylphosphine oxide group of C ₆ to C ₆₀ , an arylamine group of C ₆ to C ₆₀ , an (aryl) (heteroaryl) amine group of C ₆ to C ₆₀ , and a heteroarylamine group of 5 to 60 nuclear atoms. It is substituted or unsubstituted with one or more substituents selected from the group, and in this case, when the substituents are plural, they are the same or different from each other.

The compound represented by Formula 1 according to the present invention described above may be further specified as the following compounds 1 to 152, but is not limited thereto.

In the present invention, “alkyl” refers to a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, and hexyl.

In the present invention, “alkenyl” refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

In the present invention, “alkynyl” refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon triple bonds. Examples thereof include ethynyl, 2-propynyl, etc., but are not limited thereto.

In the present invention, “cycloalkyl” refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

In the present invention, “heterocycloalkyl” refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon, preferably 1 to 3 carbons in the ring, is N, O, S Or it is substituted with a hetero atom such as Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

In the present invention, “aryl” refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, either a single ring or a combination of two or more rings. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

In the present invention, “heteroaryl” refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply pendant or condensed with each other may be included, and a form in which two or more rings are condensed with an aryl group may also be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, phenoxathienyl, indolizinyl, and indolyl ( Polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, etc., but are not limited thereto.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, where R' refers to alkyl having 1 to 40 carbon atoms and has a linear, branched, or cyclic structure. may include. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

In the present invention, “aryloxy” is a monovalent substituent represented by RO-, where R refers to aryl having 5 to 40 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, etc., but are not limited thereto.

In the present invention, “alkylsilyl” refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and includes not only mono-, but also di- and tri-alkylsilyl. In addition, “arylsilyl” refers to silyl substituted with aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as mono-, di-, and tri-arylsilyl.

In the present invention, “alkyl boron group” refers to a boron group substituted with alkyl having 1 to 40 carbon atoms, and “aryl boron group” refers to a boron group substituted with aryl having 6 to 60 carbon atoms.

In the present invention, “alkylphosphinyl group” refers to a phosphine group substituted with alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-alkylphosphinyl groups. Additionally, in the present invention, “arylphosphinyl group” refers to a phosphine group substituted with monoaryl or diaryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosphinyl groups.

In the present invention, “arylamine” refers to an amine substituted with aryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylamine.

In the present invention, “heteroarylamine” refers to an amine substituted with heteroaryl having 5 to 60 nuclear atoms, and includes mono- as well as di-heteroarylamine.

In the present invention, (aryl)(heteroaryl)amine refers to an amine substituted with aryl having 6 to 60 carbon atoms and heteroaryl having 5 to 60 nuclear atoms.

In the present invention, “condensed ring” refers to a condensed aliphatic ring having 3 to 40 carbon atoms, a fused aromatic ring having 6 to 60 carbon atoms, a fused heteroaliphatic ring having 3 to 60 nuclear atoms, a fused heteroaromatic ring having 5 to 60 nuclear atoms, It refers to a C ₃ to C ₆₀ spiro ring or a combination thereof.

<Organic electroluminescent device>

Meanwhile, the present invention provides an organic electroluminescent device (hereinafter referred to as 'organic EL device') containing the compound represented by the above-mentioned formula (1).

Specifically, the organic electroluminescent device according to the present invention, as shown in FIGS. 1 to 3, includes an anode 100, a cathode 200, and an electroluminescent device interposed between the anode and the cathode. It includes one or more organic layers 300, and at least one of the one or more organic layers includes the compound represented by Chemical Formula 1. At this time, the above compounds may be used alone, or two or more may be used in combination.

The one or more organic layer 300 may include one or more of a hole injection layer 310, a hole transport layer 320, a light emitting layer 330, an electron transport layer 340, and an electron injection layer 350, Optionally, an electron transport auxiliary layer 360 may be additionally included. At this time, at least one organic layer 300 includes the compound represented by Formula 1 above. Specifically, the organic material layer containing the compound of Formula 1 may be the electron transport layer 340 or the electron transport auxiliary layer 360.

According to one example, the one or more organic material layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and may optionally further include an electron transport auxiliary layer. The electron transport layer includes the compound represented by Formula 1 above. At this time, the compound represented by Formula 1 is included in the organic electroluminescent device as an electron transport layer material. In such an organic electroluminescent device, electrons can be easily injected from the cathode or the electron injection layer into the electron transport layer due to the compound of Formula 1, and can also quickly move from the electron transport layer to the light-emitting layer, so that the holes and electrons in the light-emitting layer The binding force is high. Therefore, the organic electroluminescent device of the present invention has excellent luminous efficiency, power efficiency, brightness, etc. In addition, the compound of Formula 1 has excellent thermal and electrochemical stability, and can improve the performance of organic electroluminescent devices.

The compound of Formula 1 may be used alone or mixed with electron transport layer materials known in the art.

In the present invention, electron transport layer materials that can be used interchangeably with the compound of Formula 1 include electron transport materials commonly known in the art. Non-limiting examples of usable electron transport materials include oxazole-based compounds, isoxazole-based compounds, triazole-based compounds, isothiazole-based compounds, oxadiazole-based compounds, thiadiazole-based compounds, perylene ( perylene)-based compounds, aluminum complexes (e.g. Alq _3, tris(8-quinolinolato)-aluminium), gallium complexes (e.g. Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. These can be used alone or two or more types can be used together.

In the present invention, when the compound of Formula 1 and the electron transport layer material are mixed, their mixing ratio is not particularly limited and can be appropriately adjusted within a range known in the art.

According to another example, the one or more organic material layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and the electron transport auxiliary layer includes the compound represented by Formula 1. Includes. At this time, the compound represented by Formula 1 is included in the organic electroluminescent device as an electron transport auxiliary layer material. The compound represented by Formula 1 has high triplet energy. For this reason, when the compound of Formula 1 is included as an electron transport auxiliary layer material, the efficiency of the organic electroluminescent device can be increased due to the triplet-triplet fusion (TTF) effect. Additionally, the compound of Formula 1 can prevent excitons or holes generated in the light-emitting layer from diffusing into the electron transport layer adjacent to the light-emitting layer. Accordingly, the number of excitons contributing to light emission in the light-emitting layer can be increased to improve the light-emitting efficiency of the device, and the durability and stability of the device can be improved to effectively increase the lifespan of the device.

The compound of Formula 1 may be used alone or mixed with materials for the electron transport layer auxiliary layer known in the art.

In the present invention, the electron transport auxiliary layer material that can be mixed with the compound of Formula 1 includes electron transport materials commonly known in the art, such as oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives (e.g. , BCP), heterocyclic derivatives containing nitrogen, etc., but are not limited thereto.

The structure of the organic electroluminescent device of the present invention described above is not particularly limited, but for example, the anode 100, one or more organic layer 300, and cathode 200 may be sequentially stacked on a substrate (FIGS. 1 to 1) 3). In addition, although not shown, it may have a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.

According to one example, as shown in FIG. 1, the organic electroluminescent device includes an anode 100, a hole injection layer 310, a hole transport layer 320, a light emitting layer 330, an electron transport layer 340, and a cathode on a substrate. (200) may have a sequentially stacked structure. Optionally, as shown in FIG. 2, an electron injection layer 350 may be positioned between the electron transport layer 340 and the cathode 200. Additionally, an auxiliary electron transport layer 360 may be located between the light emitting layer 330 and the electron transport layer 340 (see FIG. 3).

The organic electroluminescent device of the present invention contains a It can be manufactured by forming an organic material layer and an electrode using materials and methods known in the technical field.

The organic material layer may be formed by vacuum deposition or solution application. Examples of the solution application method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

The substrate that can be used in the present invention is not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.

Additionally, examples of anode materials include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; Conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, but are not limited thereto.

Additionally, examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, or lead, or alloys thereof; and multilayer structure materials such as LiF/Al or LiO ₂ /Al, etc., but are not limited thereto.

Additionally, the hole injection layer, hole transport layer, light emitting layer, and electron injection layer are not particularly limited, and common materials known in the art can be used.

Hereinafter, the present invention will be described in detail through examples. However, the following examples only illustrate the present invention, and the present invention is not limited by the following examples.

[Preparation Example 1] - Synthesis of compound Core 1

4-chloro-6-(3-chlorophenyl)-2-phenylpyrimidine 100 g (332.0 mmol), 2-([1,1':2',1''-terphenyl]-3'-yl)-4,4 , 130.1 g (365.2 mmol) of 5,5-tetramethyl-1,3,2-dioxaborolane, 19.2 g (16.6 mmol) of Pd(PPh ₃ ) ₄ , and 138.21 g (664.0 mmol) of K ₂ CO ₃ were added to Tol 600 ml, 200 ml of EtOH and 200 ml of H ₂ O were added, heated, refluxed, and stirred for 5 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO ₄ was added to remove moisture, and then filtered. After filtering, the solvent in the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and the solid was filtered and dried to obtain 91.7 g (yield 55.8%) of compound Core 1.

Mass : [(M+H) ⁺ ] : 494

[Preparation Example 2] - Synthesis of compound Core 2

Instead of the materials used in Preparation Example 1, 100 g (332.0 mmol) of 4-chloro-6-(3-chlorophenyl)-2-phenylpyrimidine and 2-([1,1':3',1''-terphenyl]- 5'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 130.1 g (365.2 mmol), Pd(PPh ₃ ) ₄ 19.2 g (16.6 mmol), K ₂ CO ₃ 91.8 g ( 664.1 mmol), 600 ml of Tol, 200 ml of EtOH, and 200 ml of H ₂ O were used in the same manner as Preparation Example 1 to obtain 111.7 g of compound Core 2 (yield 68.0%).

Mass : [(M+H) ⁺ ] : 494

[Preparation Example 3] - Synthesis of compound Core 3

Instead of the materials used in Preparation Example 1, 4-chloro-6-(3-chlorophenyl)-2-phenylpyrimidine 100 g (332.0 mmol), 2-([1,1':2',1''-terphenyl]- 4'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 130.1 g (365.2 mmol), Pd(PPh ₃ ) ₄ 19.2 g (16.6 mmol), K ₂ CO ₃ 91.8 g ( 664.0 mmol), 600 ml of Tol, 200 ml of EtOH, and 200 ml of H ₂ O were used in the same manner as Preparation Example 1 to obtain 101.6 g (yield 61.8%) of compound Core 3.

Mass : [(M+H) ⁺ ] : 494

[Preparation Example 4] - Synthesis of compound Core 4

Instead of the materials used in Preparation Example 1, 2,4-dichloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine 50 g (158.2 mmol), 2-([1 ,1':3',1''-terphenyl]-5'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 62.0 g (174.0 mmol), Pd(PPh ₃ ) ₄ Compound Core 4 was prepared in the same manner as in Preparation Example 1, except that 9.1 g (7.9 mmol), K ₂ CO ₃ 43.7 g (316.3 mmol), Tol 300 ml, EtOH 100 ml, and H ₂ O 100 ml were used, respectively. 43.2 g (yield 57.8%) was obtained.

Mass : [(M+H) ⁺ ] : 509

[Preparation Example 5] - Synthesis of compound Core 5

Instead of the materials used in Preparation Example 1, 2-chloro-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 50.0 g (165.5 mmol), 4,4,5,5-tetramethyl-2 -(triphenylen-2-yl)-1,3,2-dioxaborolane 64.5 g (190.7 mmol), Pd(PPh ₃ ) ₄ 9.6 g (8.3 mmol), K ₂ CO ₃ 45.7 g (331.0 mmol). 48.7 g of compound Core 5 (yield 59.6%) was obtained in the same manner as Preparation Example 1, except that 300 ml of 1,4-Tol, 100 ml of EtOH, and 100 ml of H ₂ O were used, respectively.

Mass : [(M+H) ⁺ ] : 493

[Preparation Example 6] - Synthesis of compound Core 6

Instead of the materials used in Preparation Example 1, 4-chloro-6-(3-chlorophenyl)-2-phenylpyrimidine 50.0 g (166.0 mmol), 2-([1,1':2',1'':2'',1'''-quaterphenyl]-3''-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 79.0 g (182.6 mmol), Pd(PPh ₃ ) ₄ 9.6 g (8.3 mmol), K ₂ CO ₃ 45.9 g (332.0 mmol), Tol 300 ml, EtOH 100 ml, and H ₂ O 100 ml were carried out in the same manner as Preparation Example 1, and 43.4 g (43.4 g) of compound Core 6 ( Yield 45.8%) was obtained.

Mass : [(M+H) ⁺ ] : 570

[Preparation Example 7] - Synthesis of compound Core 7

Instead of the materials used in Preparation Example 1, 2-chloro-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 25.0 g (82.7 mmol), 2-(4-(9,9-dimethyl -9H-fluoren-3-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 43.0 g (91.0 mmol), Pd( PPh ₃ ) ₄ 4.8 g (4.1 mmol), K ₂ CO ₃ 22.9 g (165.5 mmol), 150 ml Tol, 50 ml EtOH, and 50 ml H ₂ O were used in the same manner as Preparation Example 1. Compound Core 7 was obtained in 17.9 g (yield 35.3%).

Mass : [(M+H) ⁺ ] : 611

[Preparation Example 8] - Synthesis of compound Core 8

Instead of the materials used in Preparation Example 1, 2,4-dichloro-6-phenyl-1,3,5-triazine 50.0 g (221.1 mmol), 2-([1,1':3',1''-terphenyl ]-4'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 86.7 g (243.3 mmol), Pd(PPh ₃ ) ₄ 12.8 g (11.1 mmol), K ₂ CO ₃ 61.1 36.9 g (yield 39.7%) of compound Core 8 was obtained in the same manner as Preparation Example 1, except that g (442.3 mmol), 300 ml of Tol, 100 ml of EtOH, and 100 ml of H ₂ O were used, respectively.

Mass : [(M+H) ⁺ ] : 419

[Preparation Example 9] - Synthesis of compound Core 9

Instead of the materials used in Preparation Example 1, 50.0 g (165.5 mmol) of 2-chloro-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine, 2-([1,1':3',1''-terphenyl]-4'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 64.8 g (182.0 mmol), Pd(PPh ₃ ) ₄ 9.6 g (8.3 mmol) , K ₂ CO ₃ 45.9 g (332.0 mmol), Tol 300 ml, EtOH 100 ml, and H ₂ O 100 ml were carried out in the same manner as Preparation Example 1, and 45.3 g of compound Core 9 (yield 51.5%) was obtained. ) was obtained.

Mass : [(M+H) ⁺ ] : 495

[Preparation Example 10] - Synthesis of compound Core 10

Instead of the materials used in Preparation Example 1, 2-chloro-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 50 g (165.5 mmol), 2-([1,1':2',1''-terphenyl]-4'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 64.8 g (182.0 mmol), Pd(PPh ₃ ) ₄ 9.6 g (8.3 mmol) , K ₂ CO ₃ 45.7 g (331.0 mmol), Tol 300 ml, EtOH 100 ml, and H ₂ O 100 ml were carried out in the same manner as Preparation Example 1, and 48.6 g of compound Core 10 (yield 59.2%) ) was obtained.

Mass : [(M+H) ⁺ ] : 495

[Preparation Example 11] - Synthesis of compound Core 11

Instead of the materials used in Preparation Example 1, 2-chloro-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 50 g (165.5 mmol), 2-([1,1':3',1''-terphenyl]-5'-yl-2,2'',3,3'',4,4'',5,5'',6,6''-d10)-4,4, 5,5-tetramethyl-1,3,2-dioxaborolane 64.8 g (182.0 mmol), Pd(PPh ₃ ) ₄ 9.6 g (8.3 mmol), K ₂ CO ₃ 45.7 g (331.0 mmol), Tol 300 ml, EtOH 100ml , 52.9 g of compound Core 11 (yield 63.2%) was obtained in the same manner as Preparation Example 1, except that 100 ml of H ₂ O were used, respectively.

Mass : [(M+H) ⁺ ] : 505

[Preparation Example 12] - Synthesis of compound Core 12

Instead of the materials used in Preparation Example 1, 40 g (132.8 mmol) of 4-chloro-6-(3-chlorophenyl)-2-phenylpyrimidine, 2-(4,4''-di-tert-butyl-[1,1 ':3',1''-terphenyl]-5'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 68.4 g (146.1 mmol), Pd(PPh ₃ ) ₄ 7.7 g (6.6 mmol), K ₂ CO ₃ 36.7 g (265.6 mmol), Tol 240 ml, EtOH 80 ml, H ₂ O 80 ml were carried out in the same manner as Preparation Example 1, and 48.7 g of compound Core 12 was obtained. (yield 60.4%) was obtained.

Mass : [(M+H) ⁺ ] : 606

[Preparation example 13]

<Step 1> Synthesis of 2-(5-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine

Instead of the materials used in Preparation Example 1, 60 g (224.2 mmol) of 3-bromo-5-chloro-1,1'-biphenyl, 2,4-diphenyl-6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1,3,5-triazine 80.6 g (224.2 mmol), Pd(PPh ₃ ) ₄ 13.0 g (11.2 mmol), K ₂ CO ₃ 62.0 g (448.5 mmol), 2-(5-chloro-[1,1'-biphenyl]-3-yl) _- 45.1 g (yield 47.9%) of 4,6-diphenyl-1,3,5-triazine was obtained.

Mass : [(M+H) ⁺ ] : 419

<Step 2> 4,4,5,5-tetramethyl-2-(6-(naphtho[2,1-b]benzofuran-10-yl)-[1,1'-biphenyl]-2-yl)-1 ,Synthesis of 3,2-dioxaborolane

2-(5-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine 45.1 g (105.5 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 32.7 g (128.9 mmol), Pd(dppf)Cl ₂ 3.9 g (5.4 mmol), KOAc 31.6 g (322.2 mmol) and 5.1 g (10.7 mmol) of Xphos were added to 450 ml of 1,4-Dioxane and heated to reflux for 6 hours. After completion of the reaction, 1,4-Dioxane was removed by concentration under reduced pressure, purified by column chromatography using dichloromethane and hexane, the solid was filtered, and 2,4-diphenyl-6-(5-(4,4, 30.6 g (55.7% yield) of 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-3-yl)-1,3,5-triazine was obtained.

Mass : [(M+H) ⁺ ] : 511

<Step 3> Synthesis of compound Core 13

Instead of the materials used in Preparation Example 1, 4-chloro-6-(3-chlorophenyl)-2-phenylpyrimidine 16 g (53.1 mmol), 2,4-diphenyl-6-(5-(4,4,5,5 -tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-3-yl)-1,3,5-triazine 29.6 g (58.4 mmol), Pd(PPh ₃ ) ₄ Compound Core was prepared in the same manner as in Preparation Example 1, except that 3.1 g (2.7 mmol), K ₂ CO ₃ 14.7 g (106.3 mmol), Tol 96 ml, EtOH 32 ml, and H ₂ O 32 ml were used, respectively. 12 was obtained in 17.0 g (yield 64.6%).

Mass : [(M+H) ⁺ ] : 650

[Preparation example 14]

<Step 1> Synthesis of 10-(6-chloro-[1,1'-biphenyl]-2-yl)naphtho[2,1-b]benzofuran

Instead of the materials used in Preparation Example 1, 50 g (18.7 mmol) of 2-bromo-6-chloro-1,1'-biphenyl and 49.0 g (186.9 mmol) of naphtho[2,1-b]benzofuran-10-ylboronic acid were used. _{, Preparation Example 1 and} The same procedure was performed to obtain 46.9 g (62.0% yield) of 10-(6-chloro-[1,1'-biphenyl]-2-yl)naphtho[2,1-b]benzofuran.

Mass : [(M+H) ⁺ ] : 404

<Step 2> 4,4,5,5-tetramethyl-2-(6-(naphtho[2,1-b]benzofuran-10-yl)-[1,1'-biphenyl]-2-yl)-1 ,Synthesis of 3,2-dioxaborolane

10-(6-chloro-[1,1'-biphenyl]-2-yl)naphtho[2,1-b]benzofuran 46.9 g (115.8 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 35.3 g (139.0 mmol), Pd(dppf)Cl ₂ 4.2 g (5.8 mmol), KOAc 34.1 g (347.5 mmol) , 5.5 g (11.6 mmol) of Xphos was added to 470 ml of 1,4-Dioxane and heated to reflux for 6 hours. After completion of the reaction, 1,4-Dioxane was removed by concentration under reduced pressure, and then purified by column chromatography using dichloromethane and hexane. The solid was filtered and dried to obtain 4,4,5,5-tetramethyl-2-(6 33.8 g (yield 58.8%) of -(naphtho[2,1-b]benzofuran-10-yl)-[1,1'-biphenyl]-2-yl)-1,3,2-dioxaborolane was obtained.

Mass : [(M+H) ⁺ ] : 496

<Step 3> Synthesis of compound Core 14

Instead of the materials used in Preparation Example 1, 2-chloro-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 18.0 g (59.6 mmol), 4,4,5,5-tetramethyl-2 -(6-(naphtho[2,1-b]benzofuran-10-yl)-[1,1'-biphenyl]-2-yl)-1,3,2-dioxaborolane 32.5 g (65.5 mmol), Pd( PPh ₃ ) ₄ 3.4 g (3.0 mmol), K ₂ CO ₃ 16.5 g (119.1 mmol), 100 ml Tol, 35 ml EtOH, and 35 ml H ₂ O were used in the same manner as Preparation Example 1. Compound Core 7 was obtained in 22.2 g (yield 58.6%).

Mass : [(M+H) ⁺ ] : 635

[Synthesis Example 1] Synthesis of Compound 1

Compound Core1 of [Preparation Example 1] 25.0 g (1eq, 51.0 mmol), 4,4,5,5-tetramethyl-2-(spiro[cyclohexane-1,9'-fluoren]-4'-yl)-1, 3,2-dioxaborolane 20.0 g (1.1eq, 55.6 mmol), Pd(OAc) ₂ 0.3 g (0.03eq, 0.15 mmol), Cs ₂ CO ₃ 32.9 g (2.0eq, 101.0 mmol), Xphos 1.4 g (0.6eq) 3.0 mmol) was added to 150ml of Toluene, 50ml of EtOH, and 50ml of H ₂ O and heated to reflux for 4 hours for reaction. After completion of the reaction, the organic layer was extracted with toluene, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and recrystallization was performed with toluene acetone to obtain 23.8 g of Compound 1 (yield 68.0%).

Mass : [(M+H) ⁺ ] : 692

[Synthesis Example 2] Synthesis of Compound 2

Compound Core2 of [Preparation Example 2] 25.0 g (1eq, 50.5 mmol), 4,4,5,5-tetramethyl-2-(spiro[cyclohexane-1,9'-fluoren]-2'-yl)-1, 3,2-dioxaborolane 20.0 g (1.10eq, 55.6 mmol), Pd(OAc) ₂ 0.3 g (0.03eq, 1.5 mmol), Cs ₂ CO ₃ 32.9 g (2.0eq, 101.0 mmol), Xphos 1.4 g (0.6eq) 3.0 mmol) was added to 150ml of Toluene, 50ml of EtOH, and 50ml of H ₂ O and heated to reflux for 4 hours for reaction. After completion of the reaction, the organic layer was extracted with toluene, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and recrystallization was performed with toluene acetone to obtain 28.7 g of Compound 2 (yield 82.0%).

Mass : [(M+H) ⁺ ] : 692

[Synthesis Example 3] Synthesis of Compound 3

Compound Core 3 of [Preparation Example 3] 25.0 g (1eq, 50.5 mmol), 2-(9,9'-spirobi[xanthen]-3-yl)-4,4,5,5-tetramethyl-1,3, 2-dioxaborolane 26.4 g (1.10eq, 55.6 mmol), Pd(OAc) ₂ 0.3 g (0.03eq, 1.5 mmol), Cs ₂ CO ₃ 32.9 g (2.0eq, 101.0 mmol), Xphos 1.4 g (0.6eq 3.0 mmol) ) was added to 150ml of Toluene, 50ml of EtOH, and 50ml of H ₂ O and heated to reflux for 4 hours to react. After completion of the reaction, the organic layer was extracted with toluene, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and recrystallization was performed with toluene acetone to obtain 25.3 g of Compound 3 (yield 62.0%).

Mass : [(M+H) ⁺ ] : 806.29

[Synthesis Example 4] Synthesis of Compound 14

Compound Core 4 of [Preparation Example 4] 25.0 g (1eq, 49.0 mmol), 4,4,5,5-tetramethyl-2-(spiro[cyclohexane-1,9'-fluoren]-2'-yl)-1 ,3,2-dioxaborolane 19.4 g (1.1eq, 53.9 mmol), Pd(OAc) ₂ 0.3 g (0.03eq, 1.5 mmol), Cs ₂ CO ₃ 31.9 g (2.0eq, 98.0 mmol), Xphos 1.4 g (0.06 eq, 2.9 mmol) was added to 150ml of Toluene, 50ml of EtOH, and 50ml of H ₂ O and heated to reflux for 6 hours for reaction. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and recrystallization was performed with toluene acetone to obtain 23.7 g of Compound 14 (yield 68.3%).

Mass : [(M+H) ⁺ ] : 707

[Synthesis Example 5] Synthesis of Compound 32

Compound Core 5 of [Preparation Example 5] 20.0 g (1eq, 40.5 mmol), 4,4,5,5-tetramethyl-2-(spiro[cyclohexane-1,9'-fluoren]-1'-yl)-1 ,3,2-dioxaborolane 16 g (1.1eq, 44.5 mmol), Pd(OAc) ₂ 0.3 g (0.03eq, 1.2 mmol), Cs ₂ CO ₃ 26.4 g (2.0eq, 81.0 mmol), Xphos 1.2 g (0.06 eq, 2.4 mmol) was added to 120ml of Toluene, 40ml of EtOH, and 40ml of H ₂ O and heated to reflux for 6 hours for reaction. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallized with toluene acetone to obtain 15.7 g of Compound 32 (yield 56.0%).

Mass : [(M+H) ⁺ ] : 691

[Synthesis Example 6] Synthesis of Compound 36

Instead of 4,4,5,5-tetramethyl-2-(spiro[cyclohexane-1,9'-fluoren]-2'-yl)-1,3,2-dioxaborolane used in Synthesis Example 2, 4,4,5 Synthesis example, except that 15.7 g (33.3 mmol) of 5-tetramethyl-2-(3-(phenanthro[9,10-b]benzofuran-11-yl)phenyl)-1,3,2-dioxaborolane was used. The same process as in 2 was performed to obtain 23.6 g of compound 36 (yield 69.0%).

Mass : [(M+H) ⁺ ] : 802

[Synthesis Example 7] Synthesis of Compound 37

10-phenyl-2 instead of 4,4,5,5-tetramethyl-2-(spiro[cyclohexane-1,9'-fluoren]-2'-yl)-1,3,2-dioxaborolane used in Synthesis Example 3 -(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-10H-phenoxazine, except that 15.4 g (33.3 mmol) was used, and Synthesis Example 3 The same process was performed to obtain 15.5 g of compound 37 (yield 64.4%).

Mass : [(M+H) ⁺ ] : 793

[Synthesis Example 8] Synthesis of Compound 38

Instead of 4,4,5,5-tetramethyl-2-(spiro[cyclohexane-1,9'-fluoren]-4'-yl)-1,3,2-dioxaborolane used in Synthesis Example 1, 4,4,5 ,5-tetramethyl-2-(3-(spiro[cyclohexane-1,9'-fluoren]-1'-yl)phenyl)-1,3,2-dioxaborolane 19.4 g (44.4 mmol) was used. , the same process as Synthesis Example 1 was performed to obtain 22.9 g of compound 38 (yield 73.7%).

Mass : [(M+H) ⁺ ] : 768

[Synthesis Example 9] Synthesis of Compound 52

Compound Core 6 of [Preparation Example 6] 20.0 g (1eq, 35.0 mmol), 4,4,5,5-tetramethyl-2-(3-(spiro[cyclohexane-1,9'-fluoren]-4'-yl )phenyl)-1,3,2-dioxaborolane 16.8 g (1.1eq, 38.5 mmol), Pd(OAc) ₂ 0.2 g (0.03eq, 1.1 mmol), Cs ₂ CO ₃ 22.8 g (2.0eq, 70.0 mmol), 1.0 g ₍ 0.06eq, 2.1 mmol) of After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallized with toluene acetone to obtain 21.3 g of Compound 52 (yield 72.0%).

Mass : [(M+H) ⁺ ] : 844

[Synthesis Example 10] Synthesis of Compound 63

Compound Core 14 of [Preparation Example 14] 22.2 g (1eq, 34.9 mmol), 4,4,5,5-tetramethyl-2-(3-(spiro[cyclohexane-1,9'-fluoren]-4'-yl )phenyl)-1,3,2-dioxaborolane 16.8 g (1.1eq, 34.6 mmol), Pd(OAc) ₂ 0.2 g (0.03eq, 1.0 mmol), Cs ₂ CO ₃ 22.7 g (2.0eq, 69.8 mmol), 1.0 g ₍ 0.06eq, 2.1 mmol) of After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallized with toluene acetone to obtain 19.7 g of Compound 63 (yield 62.0%).

Mass : [(M+H) ⁺ ] :910

[Synthesis Example 11] Synthesis of Compound 73

Compound Core 7 of [Preparation Example 7] 20.0 g (1eq, 32.7 mmol), 4,4,5,5-tetramethyl-2-(2-phenyl-9,9'-spirobi[fluoren]-7-yl)- 1,3,2-dioxaborolane 18.7 g (1.1eq, 36.0 mmol), Pd(OAc) ₂ 0.2 g (0.03eq, 1.0 mmol), Cs ₂ CO ₃ 21.3 g (2.0eq, 65.4 mmol), Xphos 1.0 g ( 0.06eq, 2.0 mmol) was added to 120ml of Toluene, 40ml of EtOH, and 40ml of H ₂ O and heated to reflux for 6 hours to react. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallized with toluene acetone to obtain 19.7 g of Compound 63 (yield 62.2%).

Mass : [(M+H) ⁺ ] :967

[Synthesis Example 12] Synthesis of Compound 74

Compound Core 8 of [Preparation Example 8] 20.0 g (1eq, 47.6 mmol), 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-xanthen]-2-yl)-1, 3,2-dioxaborolane 24.0 g (1.1eq, 52.4 mmol), Pd(OAc) ₂ 0.3 g (0.03eq, 1.4 mmol), Cs ₂ CO ₃ 31.0 g (2.0eq, 95.3 mmol), Xphos 1.4 g (0.06eq) , 2.9 mmol) was added to 120ml of Toluene, 40ml of EtOH, and 40ml of H ₂ O and heated to reflux for 6 hours to react. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallized with toluene acetone to obtain 27.8 g of compound 74 (yield 81.5%).

Mass : [(M+H) ⁺ ] :715

[Synthesis Example 13] Synthesis of Compound 93

Compound Core 9 of [Preparation Example 9] 20.0 g (1eq, 40.3 mmol), 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-xanthen]-3-yl)-1, 3,2-dioxaborolane 20.3 g (1.1eq, 44.4 mmol), Pd(OAc) ₂ 0.3 g (0.03eq, 1.2 mmol), Cs ₂ CO ₃ 26.3 g (2.0eq, 80.6 mmol), Xphos 1.2 g (0.06eq) , 2.4 mmol) was added to 120ml of Toluene, 40ml of EtOH, and 40ml of H ₂ O and heated to reflux for 6 hours for reaction. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallized with toluene acetone to obtain 21.7 g of compound 74 (yield 68.0%).

Mass : [(M+H) ⁺ ] :791

[Synthesis Example 14] Synthesis of Compound 94

Compound Core 10 of [Preparation Example 10] 20.0 g (1eq, 40.3 mmol), 4,4,5,5-tetramethyl-2-(8-phenyldibenzo[b,d]furan-2-yl)-1,3, 2-dioxaborolane 16.4 g (1.1eq, 44.4 mmol), Pd(OAc) ₂ 0.3 g (0.03eq, 1.2 mmol), Cs ₂ CO ₃ 26.3 g (2.0eq, 80.6 mmol), Xphos 1.2 g (0.06eq, 2.4 mmol) was added to 120ml of Toluene, 40ml of EtOH, and 40ml of H ₂ O and heated to reflux for 6 hours to react. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and recrystallization was performed with toluene acetone to obtain 21.7 g of compound 94 (yield 76.5%).

Mass : [(M+H) ⁺ ] :703

[Synthesis Example 15] Synthesis of Compound 95

Instead of 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-xanthen]-4-yl)-1,3,2-dioxaborolane used in Synthesis Example 13, 10-phenyl-3- Except that 23.7 g (44.4 mmol) of (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-spiro[acridine-9,9'-fluorene] was used, The same process as Synthesis Example 14 was performed to obtain 18.3 g of Compound 95 (52.3% yield).

Mass : [(M+H) ⁺ ] :866

[Synthesis Example 16] Synthesis of Compound 103

Compound Core 11 of [Preparation Example 11] 20.0 g (1eq, 39.5 mmol), 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-xanthen]-2'-yl)-1 ,3,2-dioxaborolane 19.9 g (1.1eq, 43.5 mmol), Pd(OAc) ₂ 0.3 g (0.03eq, 1.2 mmol), Cs ₂ CO ₃ 25.8 g (2.0eq, 79.0 mmol), Xphos 1.1 g (0.06 eq, 2.4 mmol) was added to 120ml of Toluene, 40ml of EtOH, and 40ml of H ₂ O and heated to reflux for 6 hours for reaction. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallized with toluene acetone to obtain 19.1 g of Compound 103 (yield 60.3%).

Mass : [(M+H) ⁺ ] :801

[Synthesis Example 17] Synthesis of Compound 109

Instead of 4,4,5,5-tetramethyl-2-(spiro[cyclohexane-1,9'-fluoren]-2'-yl)-1,3,2-dioxaborolane used in Synthesis Example 2, 4,4,5 ,5-tetramethyl-2-(3-(2-phenylspiro[fluorene-9,9'-thioxanthen]-2'-yl)phenyl)-1,3,2-dioxaborolane using 27.8 g (1eq, 43.5 mmol) Except that, the same process as Synthesis Example 2 was performed to obtain 19.1 g of compound 103 (yield 49.2%).

Mass : [(M+H) ⁺ ] :958

[Synthesis Example 18] Synthesis of Compound 123

Compound Core 12 of [Preparation Example 12] 20.0 g (1eq, 33.7 mmol), 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-xanthen]-4'-yl)-1 ,3,2-dioxaborolane 17.0 g (1.1eq, 37.1 mmol), Pd(OAc) ₂ 0.2 g (0.03eq, 1.0 mmol), Cs ₂ CO ₃ 22.0 g (2.0eq, 67.4 mmol), Xphos 1.0 g (0.06 eq, 2.0 mmol) was added to 120ml of Toluene, 40ml of EtOH, and 40ml of H ₂ O and heated to reflux for 6 hours for reaction. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallized with toluene acetone to obtain 22.7 g of Compound 123 (yield 68.8%).

Mass : [(M+H) ⁺ ] :978

[Synthesis Example 19] Synthesis of Compound 135

Instead of 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-xanthen]-3-yl)-1,3,2-dioxaborolane used in Synthesis Example 13, 4,4,5, Except that 20 g (33.7 mmol) of 5-tetramethyl-2-(3-(spiro[fluorene-9,9'-xanthen]-4'-yl)phenyl)-1,3,2-dioxaborolane was used. The same process as Synthesis Example 13 was performed to obtain 20.1 g of compound 135 (yield 68.7%).

Mass : [(M+H) ⁺ ] :867

[Synthesis Example 20] Synthesis of Compound 136

Compound Core 13 of [Preparation Example 13] 17.0 g (1eq, 26.1 mmol), 4,4,5,5-tetramethyl-2-(3-(spiro[fluorene-9,9'-xanthen]-3'-yl )phenyl)-1,3,2-dioxaborolane 15.3 g (1.1eq, 28.7 mmol), Pd(OAc) ₂ 0.2 g (0.03eq, 0.8 mmol), Cs ₂ CO ₃ 17.0 g (2.0eq, 52.2 mmol), _0.7 g (0.06eq, 1.6 mmol) of After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallized with toluene acetone to obtain 14.7 g of Compound 136 (yield 55.0%).

Mass : [(M+H) ⁺ ] :1022

[Example 1] Fabrication of a blue organic electroluminescent device

Compound 1 was purified to high purity by sublimation using a commonly known method, and then a blue organic electroluminescent device was manufactured as follows.

First, a glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1200 Å was washed with distilled water ultrasonic waves. After cleaning with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, and methanol, drying, transferring to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then cleaning the substrate for 5 minutes using UV. The substrate was transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, HT-1 + 2% HAT-CN (100 Å) / HT-1 (1400 Å) / HT-2 (50 Å) / BH + 2% BD (200 Å) / ET An organic electroluminescent device was manufactured by stacking -2 (50 Å) / Compound 1: LiQ = 1:1 (300 Å) / LiF (10 Å) / Al (1000 Å) in that order. The structures of HT-1, HAT-CN, HT-2, BH, BD, ET-2, and LiQ used here are as follows.

[Examples 2 to 20] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as Example 1, except that the materials listed in Table 1 below were used instead of Compound 1 used as the electron transport layer material in Example 1.

[Comparative Example 1] Fabrication of a blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as Example 1, except that the following compound ET-1 was used instead of Compound 1 used as the electron transport layer material in Example 1. The structure of the compound ET-1 used at this time is as follows.

[Evaluation Example 1]

The driving voltage, current efficiency, and luminescence peak at a current density of 10 mA/cm2 were measured for each blue organic electroluminescent device manufactured in Examples 1 to 20 and Comparative Example 1, and the results are shown in Table 1 below.

Sample electron transport layer material Driving voltage (V) EL peak (nm) Current efficiency (cd/A) Example 1 Compound 1 4.3 460 6.6 Example 2 compound 2 4.6 461 6.7 Example 3 Compound 3 4.4 460 6.7 Example 4 Compound 14 4.2 459 6.8 Example 5 Compound 32 4.5 461 6.5 Example 6 Compound 36 4.2 458 6.5 Example 7 Compound 37 4.6 460 6.2 Example 8 Compound 38 4.1 462 7.0 Example 9 Compound 52 4.3 458 6.3 Example 10 Compound 63 4.4 458 6.1 Example 11 Compound 73 4.3 461 6.2 Example 12 Compound 74 4.5 460 6.3 Example 13 Compound 93 4.1 462 6.4 Example 14 Compound 94 4.7 461 6.1 Example 15 Compound 95 4.6 459 6.2 Example 16 Compound 103 4.3 460 6.5 Example 17 Compound 109 4.4 458 6.4 Example 18 Compound 123 4.7 459 6.8 Example 19 Compound 135 4.6 459 6.7 Example 20 Compound 136 4.5 460 6.8 Comparative Example 1 ET-1 4.7 460 6.0

As shown in Table 1, the blue organic electroluminescent devices of Examples 1 to 20 using the compound according to the present invention as the electron transport layer material were the same as those of Comparative Example 1 using compound ET-1, a conventional electron transport layer material, as the electron transport layer. It was found to exhibit superior performance in terms of driving voltage, emission peak, and current efficiency compared to blue organic electroluminescent devices.

[Example 21] Preparation of blue organic electroluminescent device

Compound 1 was purified to high purity by sublimation using a commonly known method, and then a blue organic electroluminescent device was manufactured as follows.

A glass substrate coated with a 1500 Å thin film of ITO (indium tin oxide) was washed with distilled water ultrasonic waves. After cleaning with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, and methanol, drying, transferring to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then cleaning the substrate for 5 minutes using UV. and transferred the substrate to a vacuum evaporator.

On the ITO transparent electrode prepared as above, HT-1 + 2% HAT-CN (100 Å) / HT-1 (1400 Å) / HT-2 (50 Å) / BH + 2% BD (200 Å) / compound An organic electroluminescent device was manufactured by stacking 1 (50 Å) / ET-1: LiQ = 1:1 (300 Å) / LiF (10 Å) / Al (1000 Å) in the following order. The structures of HT-1, HAT-CN, HT-2, BH, BD, ET-2 and LiQ used at this time are as described in Example 1, and the structure of ET-1 is as described in Comparative Example 1, Omit it.

[Examples 22-40] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as Example 21, except that the materials listed in Table 2 below were used instead of Compound 1, which was used as the electron transport auxiliary layer material in Example 21.

[Comparative Examples 2 to 5] Manufacturing of blue organic electroluminescent device

A blue organic electroluminescent device was produced in the same manner as in Example 21, except that the following compounds ET-2 to ET-5 were each deposited at 50 Å instead of Compound 1, which was used as the electron transport auxiliary layer material in Example 21. Produced. The structures of the compounds ET-2, ET-3, ET-4, and ET-5 used at this time are as follows.

[Evaluation Example 2]

For the organic electroluminescent devices prepared in Examples 21 to 40 and Comparative Examples 2 to 5, the driving voltage, emission wavelength, current efficiency, and emission wavelength were measured at a current density of 10 mA/cm2, and the results are shown in the table below. It is shown in 2.

Sample Electron transport auxiliary layer material Driving voltage (V) EL peak (nm) Current efficiency (cd/A) Example 21 Compound 1 4.1 460 6.7 Example 22 compound 2 4.4 461 6.6 Example 23 Compound 3 4.1 462 7.0 Example 24 Compound 14 4.4 460 6.8 Example 25 Compound 32 4.2 461 6.7 Example 26 Compound 36 4.0 462 7.1 Example 27 Compound 37 3.8 459 7.3 Example 28 Compound 38 4.4 458 6.3 Example 29 Compound 52 3.9 459 6.9 Example 30 Compound 63 4.0 462 7.2 Example 31 Compound 73 4.3 463 6.2 Example 32 Compound 74 4.1 458 6.3 Example 33 Compound 93 4.2 460 6.5 Example 34 Compound 94 4.7 460 6.6 Example 35 Compound 95 3.9 459 7.0 Example 36 Compound 103 4.2 460 6.8 Example 37 Compound 109 4.0 458 6.7 Example 38 Compound 123 3.9 459 6.9 Example 39 Compound 135 3.7 460 7.3 Example 40 Compound 136 4.1 462 7.0 Comparative Example 2 ET-2 4.7 460 6.0 Comparative Example 3 ET-3 5.0 461 5.3 Comparative Example 4 ET-4 4.6 460 6.1 Comparative Example 5 ET-5 5.1 462 4.9

As shown in Table 2, the blue organic electroluminescent devices of Examples 21 to 40 containing the compound according to the present invention as an electron transport auxiliary layer material have higher current efficiency and driving compared to the organic electroluminescent devices of Comparative Examples 2 to 5. It was found that it showed excellent performance in terms of voltage.

100: anode, 200: cathode,
300: organic material layer, 310: hole injection layer,
320: hole transport layer, 330: light emitting layer,
340: electron transport layer, 350: electron injection layer,
360: Electron transport auxiliary layer

Claims (9)

Compound represented by Formula 1:
[Formula 1]

(In Formula 1 above,
X ₁ to X _{3 are} the same or different from each other and are each independently N or C(R ₃ ), provided that at least two of X ₁ to
a is 2 or 3,
A plurality of R ₁ is the same or different from each other, and each independently represents deuterium, a halogen group, a cyano group, a nitro group, an amino group, a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group of 3 to 40 nuclear atoms, and C ₆ to It is selected from the group consisting of an aryl group of C ₆₀ and a heteroaryl group of 5 to 60 nuclear atoms, or is condensed with an adjacent group to form a condensed ring,
Ar ₁ is hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , C ₆ to C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) amine group and hetero of 5 to 60 nuclear atoms selected from the group consisting of an arylamine group,
n is an integer from 0 to 5,
L ₁ is a single bond or is selected from the group consisting of a C ₁ ~ C ₆₀ alkylene group, a C ₆ ~ C ₆₀ arylene group, and a heteroarylene group with 5 to 60 nuclear atoms,
Y ₁ is selected from the group consisting of O, S, C(R ₄ )(R ₅ ) and N(R ₆ ),
Y ₂ is a single bond or selected from the group consisting of O, S, C(R ₇ )(R ₈ ) and N(R ₉ ),
b is an integer from 0 to 7,
R ₂ to R ₉ are the same or different from each other, and each independently represents hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl ) is selected from the group consisting of an amine group and a heteroarylamine group having 5 to 60 nuclear atoms, or is condensed with an adjacent group to form a condensed ring,
The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, _alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, Arylphosphine group, arylphosphine oxide group, arylamine group, (aryl)(heteroaryl)amine group and heteroarylamine group, the cycloalkyl group of R ₁ , heterocycloalkyl group, aryl group, heteroaryl group and condensed ring, The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl of R ₂ to R ₉ A boron group, an arylphosphine group, an arylphosphine oxide group, an arylamine group, (aryl)(heteroaryl)amine group, a heteroarylamine group, and a condensed ring, and the alkylene group, arylene group, and heteroarylene of L ₁ The groups are each independently deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group , heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group. Period, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphos Pin group, C ₆ to C ₆₀ arylphosphine oxide group, C ₆ to C ₆₀ arylamine group, C ₆ to C ₆₀ (aryl) (heteroaryl) amine group and heteroarylamine with 5 to 60 nuclear atoms. It is substituted or unsubstituted with one or more substituents selected from the group consisting of groups, or the substituents condense with adjacent groups to form a condensed ring, and in this case, when the substituents are plural, they are the same or different from each other. According to paragraph 1,
The compound represented by Formula 1 is represented by the following Formula 2 or 3:
[Formula 2]

[Formula 3]

(In Formulas 2 and 3 above,
_{X 1 to ​ ​ ​ ​}
c1 and c2 are each integers from 0 to 5,
d is 0 or 1,
Q ₁ to Q ₆ are the same or different from each other and are each independently N or C(Ar ₆ ), provided that at least one of Q ₁ to Q ₆ is N,
R _10, R ₁₁ and Ar ₂ to Ar ₆ are the same or different from each other, and each independently represents deuterium, halogen, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) is selected from the group consisting of an amine group and a heteroarylamine group having 5 to 60 nuclear atoms, or is condensed with an adjacent group to form a condensed ring,
Ar ₂ to Ar ₆ alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl Boron group, arylphosphine group, arylphosphine oxide group, arylamine group, (aryl)(heteroaryl)amine group, heteroarylamine group and condensed ring are each independently deuterium, halogen, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ Substituted or unsubstituted with one or more substituents selected from the group consisting of a C ₆₀ arylamine group, a C ₆ to C ₆₀ (aryl) (heteroaryl) amine group, and a heteroarylamine group having 5 to 60 nuclear atoms, or The substituents condense with adjacent groups to form a condensed ring, and in this case, when the substituents are plural, they are the same or different from each other). According to paragraph 1,
remind Compounds wherein the moiety is selected from the group consisting of the following moieties Mo1-1 to Mo1-15:


(In the moiety Mo1-1 to Mo1-15,
d, m1 and m2 are 0 or 1 respectively,
c3 to c7 are each an integer from 0 to 5, provided that 1≤c3+c4≤10, 1≤c5+c6≤10,
c8 is an integer from 0 to 4,
c9 is an integer from 0 to 8,
c10 is an integer from 0 to 6,
R ₁₂ and R ₁₃ are the same as or different from each other, and are each independently selected from the group consisting of a cyano group, an alkyl group of C ₁ to C ₄₀ and a heteroaryl group of 5 to 60 nuclear atoms,
Z ₁ is selected from the group consisting of O, S, C(R ₁₅ )(R ₁₆ ) and N(R ₁₇ ),
Z ₂ to Z ₁₃ are the same or different from each other, and are each independently a single bond or selected from the group consisting of O, S, C(R ₁₈ )(R ₁₉ ) and N(R ₂₀ ),
X ₄ to X _{7 are} the same or different from each other and are each independently N or C(R ₂₁ ), provided that at least one of X ₄ to
Ring Cy1 to Cy3 are the same or different from each other, and are each independently a fused aromatic ring of C ₆ to C ₃₀ or a fused heteroaromatic ring of 5 to 30 nuclear atoms,
One or more R ₁₄ are the same or different from each other, and are each independently selected from the group consisting of an aryl group of C ₆ to C ₃₀ and a heteroaryl group of 5 to 30 nuclear atoms,
R ₁₅ to R ₂₁ are the same or different from each other, and are each independently hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) selected from the group consisting of an amine group and a heteroarylamine group having 5 to 60 nuclear atoms, or condensed with an adjacent group to form a condensed ring). According to paragraph 1,
Wherein L ₁ is a single bond or a compound selected from the group consisting of the following linker groups L1-1 to L1-3:

(In the linker groups L1-1 to L1-3,
e is an integer from 0 to 4,
R ₂₂ is hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cyclo Alkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , aryl with C ₆ to C ₆₀ Oxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl Phosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) amine group, and heteroaryl with 5 to 60 nuclear atoms selected from the group consisting of amine groups). According to paragraph 1,
remind Compounds wherein the moiety is selected from the group consisting of the following moieties Mo3-1 to Mo3-17:




(In the moieties Mo3-1 to Mo3-17,
Y ₁ , b and R ₂ are each as defined in clause 1,
CyA and CyB are the same or different from each other, and are each independently selected from the group consisting of a fused aromatic ring of C ₆ to C ₃₀ and a fused heteroaromatic ring of 5 to 30 nuclear atoms,
b1 is an integer from 0 to 5,
b2 is an integer from 0 to 3,
f is an integer from 0 to 8,
f1 is an integer from 0 to 6,
f2 is an integer from 0 to 4,
R ₂₃ is hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ Cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , C ₆ to C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) amine group and hetero of 5 to 60 nuclear atoms selected from the group consisting of an arylamine group,
The condensed aromatic ring and condensed heteroaromatic ring of CyA and CyB are each independently deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) Substituted or unsubstituted with one or more substituents selected from the group consisting of amine groups and heteroarylamine groups having 5 to 60 nuclear atoms, wherein when the substituents are plural, they are the same or different from each other). According to paragraph 1,
The compound represented by Formula 1 is represented by any one of the following Formulas 4 to 37:
[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

[Formula 22]

[Formula 23]

[Formula 24]

[Formula 25]

[Formula 26]

[Formula 27]

[Formula 28]

[Formula 29]

[Formula 30]

[Formula 31]

[Formula 32]

[Formula 33]

[Formula 34]

[Formula 35]

[Formula 36]

[Formula 37]

(In Formulas 4 to 37,
_{X 1 to ​ ​ ​}
CyA and CyB are the same or different from each other, and are each independently selected from the group consisting of a fused aromatic ring of C ₆ to C ₃₀ and a fused heteroaromatic ring of 5 to 30 nuclear atoms,
b1 is an integer from 0 to 5,
b2 is an integer from 0 to 3,
c1 and c2 are each integers from 0 to 5,
d is 0 or 1,
f is an integer from 0 to 8,
f1 is an integer from 0 to 6,
f2 is an integer from 0 to 4,
Q ₁ to Q ₆ are the same or different from each other and are each independently N or C(Ar ₆ ), provided that at least one of Q ₁ to Q ₆ is N,
R _10, R ₁₁ and Ar ₂ to Ar ₆ are the same or different from each other, and each independently represents deuterium, halogen, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) is selected from the group consisting of an amine group and a heteroarylamine group having 5 to 60 nuclear atoms, or is condensed with an adjacent group to form a condensed ring,
R ₂₃ is hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ Cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , C ₆ to C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ Arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group, C ₆ ~ C ₆₀ arylamine group, C ₆ ~ C ₆₀ (aryl) (heteroaryl) amine group and hetero of 5 to 60 nuclear atoms selected from the group consisting of an arylamine group,
CyA and the condensed aromatic ring and condensed heteroaromatic ring of CyA, and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, and aryloxy group of Ar ₂ to Ar ₆ Group, alkyl silyl group, aryl silyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, aryl amine group, (aryl) (heteroaryl) amine group, heteroaryl amine group and condensed ring are each Independently deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nucleus Heterocycloalkyl group with 3 to 40 atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, Consists of an arylphosphine oxide group of C ₆ to C ₆₀ , an arylamine group of C ₆ to C ₆₀ , an (aryl) (heteroaryl) amine group of C ₆ to C ₆₀ , and a heteroarylamine group of 5 to 60 nuclear atoms. Substituted or unsubstituted with one or more substituents selected from the group, wherein when the substituents are plural, they are the same or different from each other). According to paragraph 1,
The compound represented by Formula 1 is selected from the group consisting of the following compounds 1 to 152:









. anode; cathode; It includes one or more organic layers interposed between the anode and the cathode,
An organic electroluminescent device wherein at least one of the one or more organic layers includes the compound according to any one of claims 1 to 7. According to clause 8,
An organic electroluminescent device in which the organic layer containing the compound is an electron transport layer or an electron transport auxiliary layer.

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